Chemical and Pharmaceutical Bulletin

Stereochemical Studies. X. Effects of Neighboring Functional Groups on 1, 2-Asymmetric Induction in the Reduction of Propiophenone Derivatives with Sodium …

K KOGA, SI YAMADA

Index: Koga,K.; Yamada,S.-I. Chemical and Pharmaceutical Bulletin, 1972 , vol. 20, # 3 p. 526 - 538

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Citation Number: 31

Abstract

Effects of neighboring functional groups on 1, 2-asymmetric induction in sodium borohydride reduction were examined with eight kinds of ketones (I-VIII) having functional groups, such as-NH 2 HCl,-OH, and-OCH 3, at a-and/or β-positions to the carbonylgroup. It was recognized that the stereochemical course of the reduction was highlydependent on the position of these functional groups, ie erythro-rich products were obtained in reduction of ...